Process for rendering textile materials antistatic



United States Patent 3,108,011 PROCESS FOR RENDERING TEXTILE MATERIALS ANTISTATIC Herbert Frotscher, Dusseldorf-Bcnrath, Germany, as= signor to Bohme Fettchemie G.m.b.H., Dusseldorf, Germany, a corporation of Germany No Drawing. Filed Nov. 10, 1960, Ser. No. 68,356 Claims priority, application Germany Nov. 24, 1959 Claims. (Cl. 117-621) This invention relates to a process for rendering textile materials antistatic by treating the textile materials with the reaction product of water-soluble polyamines containing polyalkylene oxide radicals with compounds containing more than one epoxide and/ or halohydrin group.

There is described in the commonly-assigned, copending application Serial No. 836,063, filed August 26, 1959, a process for permanently imparting an antistatic finish to textile materials, such as fibers, threads, foils, films, ribbons, tubes, fleeces, felts, Woven or knit textile materials made of substances such as polyacrylonitrile, polyesters, polyamides, cellulose esters, wool, silk, cotton, rayon and mixtures thereof, by treating said textile materials with alkaline aqueous solutions of products obtained by reacting water-soluble polyamines containing polyalkylene oxide radicals with compounds which contain more than one epoxide group and/ or halohydrin group, and subsequently drying these treated materials at normal or elevated temperatures. In the case of an immersion procedure, this process is carried out in an alkaline bath. The materials absorb only that amount of the active products which are contained in the solution remaining on the fiber after squeeze-drying.

It is an objecltjgof the invention to provide a novel process for rendering textile materials antistatic even after numerous washings. p,

It is another object of the invention to provide a novel process for rendering textile materials antistatic by treatment-with acidic aqueous solutions of the reaction productbf water-soluble polyamines containing polyalkylene oxide radicals with compounds containing more than one epoxide and/ or halohydrin group.

These and other objects and advantages of the invention will become obvious from the following detailed description.

The process of the invention comprises impregnating the textile material with an aqueous solution of the reaction product of water-soluble amines containing polyalkylene oxide radicals and compounds containing more than one epoxide and/or halohydrin group having a pH value less than 7, preferably less than 6, and then treating said textile material with an aqueous bath having a pH greater than 7.5 to harden the deposited amine product. The textile material may then be rinsed and dried by known methods at room temperature or elevated temperatures. The thus treated material may be further treated with a scrooping agent such as octadecyl pyridinium sulfate in a bath to improve the feel. of the material. i

3,198,111 1 Patented Oct. 22, 1963 A simplified flow diagram of the process is as follows:

Application at elevated temperatures Sodium carbonate Hardening of the coating Rinsing Centr. iuging Drying The impregnation of the textile material is conducted for a period of 5 to 100 minutes, usually 10 to 20 minutes is sufiicient. The temperature of the acid bath is 30 to 100 0, preferably about to C. In order to obtain a rapid and complete deposition on the textile material, it is often advantageous to add small amounts of an anion-active compound to the bath. Suitable anion-active compounds are, for example, alkyl sulfates 8 to 18 carbon atoms, such as lauryl sulfate, oleyl sulfate, and octadecyl sulfate, alkyl benzene sulfonates' such as dodecyl benzene sulfonate, Turkey Red oil, and other known anion-active substances.

The pH of the bath is adjusted to a pH below 7 by the addition of any water-soluble inorganic or organic acid. Examples of such acids are sulfuric acid, phosphoric acid, formic acid, acetic acid, oxalic acid, succinic acid, citric acid and lactic acid.

The alkaline bath has a pH greater than 7.5, preferably between 8 and 11, and is maintained at a temperature between 50 and C., preferably 70 to 95 C. The treatment of the textile material is usually for a period of 10 to 100 minutes.

The pH of the alkaline bath is adjusted to above 7.5 by the addition of any water-soluble organic or inorganic base. Examples of suitable bases are alkali metal hydroxides and carbonates, such as potassium hydroxide, sodium hydroxide, sodium bicarbonate, sodium carbonate, and potassium carbonate and amines such as triethanolamine and pyridine.

Instead of using separate acid and alkaline baths, the process of the invention may be carried out in the same bath by adding the base to the acid bath to adjust the pH to greater than 7.5. It may also be performed directly in a dyeing bath after dyeing in acid bath with dispersion dyes, for example, or after dyeing with basic dyes. The antistatic finish may also be applied to the textile material before dyeing because the said finish is stable under any dyeing conditions, even at the boiling point of the dye bath.

The concentration of water-soluble reaction product in the bath is not critical and a wide range of concentrations can be employed. It is preferable to have about 0.5 to 6% of the reaction product calculated on the basis of the weight of the textile material to be finished present in the solution.

The process of the invention is particularly suitable for finishing textile materials made of polyacrylonitrite or polyester fibers, such as Dacron and Kodel, and their mixtures with each other or any other synthetic or natural fiber. The process is primarily useful for treating loose material, yarns and knit goods, but may also be applied to woven goods. A satisfactory antistatic property which will remain after numerous washings in obtainable quantitatively even from relatively dilute baths.

The reaction products which are useful in the acid baths of the process are obtained from the reaction of water-soluble polyamines containing polyalkylene oxide groups with compounds containing more than one epoxide and/ or halohydrin group. They are more fully described in the commonly-assigned, copending application Serial No. 836,063, filed August 26, 1959.

The water-soluble polyamines containing polyalkylene oxide radicals, which are used as starting materials for the reaction products, are essentially known substances and may be obtained in accordance with known methods. For example, they may be prepared by reacting monoand/ or poly-functional derivatives of polyalkylene oxides, which contain reactive groups capable of reacting with amino groups by an exchange of hydrogen atoms, with polyamines.

The compounds used as the second starting component, that is, the compounds which contain more than one epoxide and/or halohydrin group in the molecule, include primarily epichlorohyd-rin and dichlorohydrins as well as their reactive reaction products which contain more than one epoxide and/or halohydrin group in the molecule.

Examples of mono and/or poly-functional derivatives of polyalkylene oxides of the above-indicated type are those derivatives of polyalkylene oxides which contain, as reactive groups, chlorohydrin radicals, glycidyl radicals, halogen or other radicals capable of forming anions, such as sulfuric acid radicals, alkylsulfonic acid radicals and the like. The polyalkylene oxide groups present in these compounds may be of various molecular size, but, in general, the starting materials are selected so that a total of about 3 to 70 alkylene oxide radicals are present in the molecule. Ethylene oxide is primarily suitable as an alkylene oxide; however, other cyclic oxides, such as propylene oxide or cyclohexanepxide as well as corresponding mixtures, may also be used. The alkylene oxide chains may also be interrupted, for example, by a dicarboxylic or diisocyanate radical.

Accordingly, examples of compounds which may be used as starting materials for the preparation of the substituted polyamines, and by the radicals of which the polyamines are characterized, are the following: Monoand bis-chlorohydrin ethers of polyalkylene oxides,

Monoand bis-glycidyl ethers of polyalkylene oxides,

Bis-sulfuric acid esters of polyalkylene oxides,

Dihalides of polyalkylene oxides,

Oxalkylation products of ethylene chlorohydrin,

Mono-, diand tri-halides of oxethylated glycerin,

Mono-, di-, triand tetra-halides of oxethylated pentaerythrite,

Monochlorohydrin ethers of oxalkylated alcohols,

Monoglycidyl ethers of oxalkylated alcohols,

Reaction products formed by oxethylated ethylene chlorohydrin and a diisocyanate,

Reaction products of oxethylated ethylene chlorohydrin and a dicarboxylic acid or its anhydride.

For the preparation of the starting materials, these compounds are condensed with polyamines which contain at least two nitrogen groups containing replaceable hydrogen atoms in the molecule. For this purpose, polyalkylene polyamines are preferred, but other polyamines, such as those of an aromatic nature, may also be used. Examples of such amines are the following: ethylene diamine, diethylene triamine, dipropylene triamine, triethylene tetramine, 1,4-phenylene diamine, 1,4-diamino cyclohexane and the like.

Polyalkoxylated polyamines which are derived from ldipropylene triamine have been found to be particularly suitable because they produce light-stable synthetics which are light in color.

As already mentioned, the reaction of the above-mentioned starting components for the formation of the polyalkoxylated polyamines used as starting materials is effected in accordance with known methods. In order to obtain products which are particularly suitable for the process according to the invention, the quantitative ratios of the starting materials, the chain length and the reaction conditions are preferably selected so that products are obtained which are readily water-soluble, which may be achieved without difiiculty by variation of the length of the polyalkylene oxide chains and of the amine component. It is important that the quantities of the polyamines be such that after the completed reaction the polyalkylene oxylated polyamines contain a sufiicient number of reactive amino groups which are capable of reaction with epichlorohydrin or dichlorohydrin or with the compounds containing epoxide and/or halohydrin groups.

As already mentioned, primarly epichlorohydrin and dichlorohydrin are used as the compounds which contain more than one epoxide and/or halohydrin group in the molecule. However, reaction products of these compounds which still contain reactive epoxide or halohydrin groups, such as reaction products of epichl-orohydrin or dichlorohydrin with glycols, diglycols, polyalkylene oxides, glycerine, dicarboxylic acids, polycarboxylic acids, polyvalent phenols and the like, may also be used with advantage.

The reaction of these compounds with the alkylene oxylated polyamines proceeds smoothly. It may be carried out without or in the presence of organic solvents or water as well as acid-binding substances, such as caustic soda, sodium carbonate, magnesium carbonate and the like.

In the following examples there are described several preferred embodiments to illustrate the invention. However, it should be understood that the invention is not intended to be limited to the specific embodiments.

EXAMPLE I Step A 180 kg. of liquid polyglycol 600 were placed into a vessel provided with a heating and cooling device, a reflux cooler, a thermometer and a stirring device. 2.7 kg. of tin tetrachloride were then allowed to flow slowly into the liquid at about 30 C., accompanied by stirring. The mixture was heated to 68 to 70 C. and 56 kg. of epichlorohydrin were added rapidly, accompanied by constant stirring and cooling so that the temperature of the mixture remained between 68 and 70 C. The resulting mixture was then stirred for one hour at temperatures around 70 C. The total amount of raw polyglycol-bischlorohydrin ether thus obtained was about 239 kg. kg. of the raw chlorohydrin ether were drawn otf into another vessel provided with a thermometer, reflux cooler, heating and cooling device and stirrer and having a capacity of about 600 liters, where it was admixed with 13.2 gm. of dipropylene triamine, 50 kg. of water and 28 kg. of 40% sodium hydroxide, accompanied by stirring. Thereafter, the mixture was heated to the boiling point for 45 minutes under reflux. vThe remaining amount of raw chlorohy-drin ether of polyglycol 600 in the first vessel was then added while stirring and then the resulting mixture was maintained at the boiling point for an additional 20 to 30 minutes after adding 30 kg. of water. During this period the pH of the viscous reaction product dropped to about 7.2. The reaction mixture was then vigorously cooled while adjusting the pH to 5.5 to 6 by adding about 38 kg. of aqueous hydrochloric acid. About 500 kg. of a faintly yellow, slightly cloudy highly viscous liquid were obtained which rapidly gelled at about 40 C. upon adding sodium hydroxide to obtain a distinct alkaline reaction.

Step B kg. of undyed ladies sweaters made of polyacryloru'trile yarn were dyed in a dye vat containing 750 liters of dyeing solution at 90 to 95 C., the dye bath containing, in addition to the dispersion dyes, 0.4 liter of 60% acetic acid and 0.5 kg. of a commercial anion-active scrobping agent containing about 25% active substance ctfinsisting of partially sulfonated fatty alcohols having 1.2 to 18 carbon atoms. After completion of the dye prrocedure, 0.5 kg. of the reaction product of Step A Was added to the bath and the sweaters were treated for atnother 10 to minutes at 80 to 90 C. Thereafter, 3.5 kg. of soda ash, dissolved in water, were added and the sweaters were treated for another 20 minutes at 80 to 90 C. in this bath. Subsequently, the sweaters were treated at about 30 C. in a fresh bath which contained 0.5 to 1 gm. per liter of a customary cation-active soroopting agent, octadeoyl-pyridinium sulfate. The finished sweaters exhibited a good antistatic effect which was retained even after numerous launderings. In addition, they still had a pleasant feel after several launderings and showed practically no piling effect.

EXAMPLE II Step A 180 kg. of polyglycol 600 were reacted with 56 kg. of epichlorohydrin in the presence of 2.7 kg. of tin tetrachloride, as described in Example I. After adding 13.2 kg. of dipropylene t-riamine, 35 kg. of 40% s-odium'hydroxide and 150 kg. of water, the mixture was refluxed at the boiling point for about 40 minutes. The pH of the viscous reaction mixture had dropped to 7.2 at the end of this period. The reaction mixture was then adjusted to a pH of about 5.5 with approximately 66 kg. of 10% hydrochloric acid. About 500 kg. of a cloudy, virtually colorless product were obtained which rapidly solidified into a gel at 40 to 50 C. upon being made alkaline.

The reaction may be carried out in analogous fashion, that is, in a single reaction process, in all those cases where the bis-chlorohydrin ethers or their mixtures used for the formation of the polyalkoxylated polyamines and for the subsequent reactions are identical. In this procedure it is advantageous to select the ratio of the number of chlorine atoms and the number of amino-hydrogen atoms present in the reaction mixture such that it is about 4:5 to 7:5.

Step B 50 kg. of a high bulk polyacrylonitrile yarn were treated at about 80 C. for 15 minutes in a customary yarndyeing suspension system apparatus with a circulating solution of 3000 liters of an aqueous solution containing 2 kg. of the product produced in Step A, 1 kg. of a mixture of partially sulfonated high molecular fatty alcohols having 12 to 18 canbon atoms with about 30% total content of fatty alcohols and 1.5 liter of 60% acetic acid. The weight ratio of yarn to solution is 1:60. Thereafter, 3 kg. of soda ash dissolved in water were added and the yarn was treated for another 20 minutes at about 80 C. Thereafter, the bath was cooled to about 50 C. in the customary fashion by slowly adding cold water.

After drawing off the impregnating solution, the yarn was rinsed with cold to lukewarm water which contained a scrooping agent. The finished yarn was then centrifuged and dried. The yarn had excellent antistatic properties which remained unchanged even after numerous household launderings.

EXAMPLE III A polyester curtain fabric was dyed in a winch vat with a dye bath at to C., the bath ratio being 1:40, and the dye bath containing, in addition to the dispersion dyes, 0.5 cc. per liter of 60% acetic acid and 1 to 1.5 gm. per liter of the anion-active sorooping agent used in Example I. After the dye procedure, the dye bath was modified by adding 1 gm. per liter of the product of Step A of Example II and the fabric was treated therein for 15 minutes at 80 to 90 C. Thereafter, 1.5 gm. per liter of soda ash dissolved in water were added to the same bath. Then the fabric was treated for an additional 30 minutes at about 80 C. in this bath. After drawing off the solution, the treated fabric was rinsed, centrifuged and dried. The drapery materials finished in this manner exhibited excellent antistatic properties which remained even after several launderings in a washing machine.

EXAMPLE 1V Step A parts by weight of polyglycol 1000 (0.1 mol) were melted in a vessel provided with a stirrer, thermometer and reflux cooler, and the molten mass was admixed with 2 parts by weight of boron trifluoride. 14 parts by weight of epichlorohydrin (0.15 mol) were then added. After stirring the mixture for 1 hour at 68 to 72 C., 14 parts by weight of triethylene tetramine and 70 parts by weight of water were added and the mixture was heated under reflux for about 20 minutes. 25 parts by weight of 40% sodium hydroxide were then added and the mixture was boiled for an additional 30 minutes. Thereafter, 82 parts by weight of a raw bis-chlorohydrin ether of polyglycol 600, obtained by treating 1 mol of polyglycol 600 with 2 mols of epichlorohydrin in the presence of boron trifiuoride, were added. After stirring this mixture at the boiling point for one hour, 4.6 parts by weight of epichlorohydrin were added. The reaction mixture was then stirred until the pH dropped to about 7 to 7.5. The pH was then adjusted to 5.4 to 6 with concentrated hydrochloric acid, and water was added until a total weight of 300 parts by weight was reached. A faintly yellow, cloudy, viscous liquid was obtained which rapidly gelled at 50 C. upon addition of a small amount of sodium hydroxide.

. StepB 50 kg. of a mixed yarn consisting of 70 parts of polyester fiber and 30 parts of viscous rayon are treated at a yarn-to-solution weight ratio of 1:40 in a customary yarn-dyeing suspension system apparatus with a circulating solution of 2000 liters of an aqueous solution comprising 0.8 kg. of a product obtained in Step A, 0.1 kg. of a 100% tetrapropylene benzene sulfonate, and 1.0 liter of 60% acetic acid.

The treatment began at a solution temperature of about 50 C., which was then increased in the course of 15 minutes to 80 C. The yarn was then treated at this temperature for 5 minutes. Thereafter, 1.5 kg. of soda ash dissolved in water were added and the yarn was treated for an additional 20 minutes at about 80 C. The treatment solution was then drawn off and the yarn was rinsed with cold to lukewarm water in customary fashion. The finished yarn was then centrifuged and dried. It had an excellent, laundering resistant antistatic property.

EXAMPLE V A tricot fabric consisting of 50% of polyester fiber and 50% of polyamide fiber was treated in a winch vat at a yarn-to-solution ratio of about 1:30 in a bath containing 0.8 gm. per liter of the product of Step A in Example 11. 0.2 gm. per liter of a high molecular fatty alcohol sodium sulfate with about 30% total fatty alcohol content, and 1.0 gm. per liter of 60% acetic acid.

The treatment was begun at about 50 C. and the temperature was increased to 80 to 90 C. within a period of 15 to 20 minutes. The fabric was treated at this temperature for 5 minutes. Thereafter, 1 cc. per liter of 40% sodium hydroxide was added and the fabric was treated for another 20 minutes at 80 to 90 C. The treatment solution was then drawn off while adding cold water thereto and the tricot was rinsed in customary fashion. For achieving a soft feel, the finished fabric was then treated with a cation-active scrooping agent. The finished tricot exhibited good antistatic properties which were resistant against repeated laundering as well as dry cleaning.

EXAMPLE VI Step A 290 gm. (0.3 mol) of a reaction product of 1 mol of ethylene chlorohydrin and 20 mols of ethylene oxide were heated for four hours at 120 C. in a round bottom flask provided with a reflux cooler with 31 gm. (about 0.3 mol) of diethylene triamine, accompanied by stirring. Thereafter, the reaction mixture was cooled to about 60 C., 100 gm. of water and 55 gm. of epichlorohydrin were added, and the mixture was stirred at 55 to 60 C. until the pH dropped to about 7 (1 /2 to 2 hours). The viscous product thus obtained was adjusted to a pH of 6 with hydrochloric acid and was diluted with water to a total weight of 510 gm. The solution gelatinized in the presence of an alkali.

Step B Loose material consisting of 55% of polyacrylonitrile fibers and 45% of wool was treated in a radial dyeing apparatus at a yarn-to-solution ratio of about 1:20 for 20 minutes at 80 C. with an aqueous solution containing 1 gm. per liter of the product obtained in Step A, and 0.5 gm. per liter of 60% acetic acid. Thereafter, 1 gm. per liter of sodium bicarbonate dissolved in water was added and the material was treated for another 20 minutes at 80 to 85 C. The bath was then cooled within a period of minutes to 50 C. by adding cold water, and the solution was drawn off. Then the material was rinsed at 30 C. with water containing 1 gm. per liter of a cation-active scrooping agent, centrifuged and dried. The loose material thus obtained had good spinning properties and exhibited good antistatic properties which were retained by the textile fabric produced therewith even after several launderings or dry cleaning.

EXAMPLE VII 50 kg. of a padded, undyed polyacrylonitrile yarn were treated at a yarn-to-solution ratio of about 1:60 in a customary yarn-dyeing suspension system apparatus in 3000 liters of an aqueous solution which contained, based on the weight of textile fiber, 3.5% of a product obtained in Step A of Example 11, 1% of a high molecular fatty alcohol sodium sulfate with about 40% active substance, and 1 cc. per liter of 60% acetic acid. The treatment was begun at 40 C., the temperature was raised to 90 C. over a period of minutes, and then this temperature was maintained for 5 minutes. This same bath was then modified by adding 1 gm. per liter of soda ash dissolved in water and the yarn was treated for another 20 minutes at 80 to 85 C. Thereafter, the solution was cooled to 50 C. within 20 minutes, the bath was drawn off, and the yarn Was rinsed with cold water. In a fresh bath the finished yarn was dyed in a dye bath comprising 0.5 gm. per liter of a nonyl phenol polyoxyethylate which contains about 9 ethylene oxide groups P molecule, and 0.12% of a yellow dispersion dye (l (Artisil yellow GN/Sandoz), based on the weight of yarn. The dyeing procedure was begun at 40 C. by first immersing the yarn for 10 minutes into the bath without the dye, then adding the dye and finally heating the solution within 30 minutes to 100 C. Thereafter, the yarn was dyed at the boiling temperature of the dye bath for one hour, the dye bath was slowly cooled to 50 C. over a period of 30 minutes, and the dyed yarn was rinsed in customary fashion. A uniform dyeing effect was obtained. The antistatic properties of the finished yarn were excellent. Knitted fabrics produced therewith soiled less readily than similar fabrics not finished in this manner and exhibited a reduced tendency to pill.

EXAMPLE vIII An undyed padded polyacrylonitrile fabric was provided with an antistatic finish in the same manner as in Example VII. After the intermediate rinsing step, the yarn was treated in a bath with 1% of a blue basic dye (Basacryl blue 214/ Bayer), based on the weight, of yarn, 1% of a special auxiliary agent (Levegal BAN/Bayer) and 1 cc. per liter of 60% acetic acid, again first at 40 C. for 5 minutes without the dye. The dissolved dye was then added, and the temperature was incrteased to to C. over a period of 10 to 15 minutes/J11 the course of an additional 15 to 20 minutes the tem-\ perature was increased to C. and the yarn was dyed at the boiling temperature of the solution for one hour. After completion of the dyeing procedure, the dye bath was cooled to 50 C. within 20 to 30 minutes and was then rinsed for 15 minutes at 30 to 35 C. in the presence of 1 gm. per liter of a cationic scrooping agent. The yarn was then centrifuged and dried. The dyeing effect thus obtained had the normal fastness and the yarn was satisfactorily antistatic. The textile materials produced from this yarn retained their antistatic properties even after numerous washings and chemical dry cleanings.

Various modifications of the process of the present invention may be made without departing from the spirit or scope thereof, and it is to be understood that the invention is limited only as defined in the appended claims.

I claim:

1. A process for rendering textile materials antistatic which comprises impregnating textile materials with an acidic aqueous solution of the reaction product of watersoluble polyamines containing polyalkylene oxide groups attached to the nitrogen atom and having in the molecule more than one reactive hydrogen atom attached to a nitrogen atom and compounds containing more than one member selected from the group consisting of epoxide and halohydrin radicals having a pH of less than 7, treating the impregnated textile material with a basic aqueous solution having a pH greater than 7.5 and rinsing the drying said treated textile material whereby an antistatic textile material is obtained.

2. The process of claim 1 wherein the acidic aqueous solution contains an anion-active compound.

3. The process of claim 1 wherein the pH of the acidic aqueous solution is below 6.

4. The process of claim 1 wherein the pH of the basic aqueous solution is between about 8 and about 11.

5. The process of claim 1 wherein the textile material is dyed before impregnation.

6. The process of claim 1 wherein the textile material is undyed before impregnation.

7. A process for rendering antistatic textile materials selected from the group consisting of polyacrylonitrile fibers, polyester fibers and their mixtures with each other and with other fibers which comprises impregnating said materials with an acidic aqueous solution of the reaction product of water-soluble polyamines containing polyalkylene oxide groups attached to the nitrogen atom and having in the molecule more than one reactive hydrogen atom attached to a nitrogen atom and compounds containing more than one radical selected from the group consisting of epoxide and halohydrin radicals at a pH of less than 6 and a temperature from 30 to 100 C., treating the impregnated material with a basic aqueous solution having a pH greater than 7 and a temperature from 50 to 100 C. and rinsing and drying the treated material whereby an antistatic material is obtained.

8. The process of claim 7 wherein an anionactive compound is present in the acidic aqueous solution.

9. The process of claim 7 wherein the pH of the basic aqueous solution is from 8 to 11.

10. The process of claim 7 wherein the basic aqueous solution is formed by adding sur'iicient base to the acidic aqueous solution to adjust the pH of said solution to greater than 7.5.

5 References Cited in the file of this patent UNITED STATES PATENTS 2,891,029 Coler et a1. June 16, 1959 2,897,201 Albrecht 12 July 28, 1959 10 2,930,106 Wrotnowski Mar. 29, 1960 FOREIGN PATENTS 443,632 Great Britain Feb. 17, 1936 

1. A PROCESS FOR RENDERING TEXTILE MATERIALS ANTISTATIC WHICH COMPRISES IMPREGNATING TEXTILE MATERIALS WITH AN ACIDIC AQUEOUS SOLUTION OF THE REACTION PRODUCT OF WATERSOLUBLE POLYAMINES CONTAINING POLYALKYLENE OXIDE GROUPS ATTACHED TO THE NITROGEN ATOM AND HAVING IN THE MOLECULE MORE THAN ONE REACTIVE HYDROGEN ATOM ATTACHED TO A NITROGEN ATOM AND COMPOIUNDS CONTAINING MORE THAN ONE MEMBER SELECTED FROM THE GROUP CONSISTING MORE THAN ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF EPOXIDE AND HALOHYDRIN RADICALS HAVING A PH OF LESS THAN 7, TREATING THE IMPREGNATED TEXTILE MATERIAL WITH A BASIC AQUEOUS SOLUTION HAVING A PH GREATER THAN 7.5 AND RINSING THE DRYING SAID TREATED TEXTILE MATERIAL WHEREBY AN ANTISTATIC TEXTILE MATERIAL IS OBTAINED. 